27 Answers To Your Most Pressing Digital Nomad Questions

Posted on /by Natalie Sisson/ in Business Travel

Recently I got asked by the lovely folks at BeNomad if I’d answer some questions for the digital nomads in their Slack Channel.

Little did I know that over 2 hours later I’d have written answers to every single question, and at the same time have taken a trip down memory lane to when I was fully embracing location independence.

There were so many good ones I asked if I could share a couple of them and my answers here on my blog, and happily they agreed.

So let’s dive in shall we?

Digital Nomad Lifestyle:

Q1. Do you think the digital nomad lifestyle can be for everyone or is it just for very specific kinds of people?

I actually have a Pros and Cons chart in my Suitcase Entrepreneur book to address this exact question. In short, no I don’t think it’s for everyone.

You need to be comfortable with change, with making constant decisions on where you travel to, sleep, eat etc. You need to get used to things not going as planned, you need to be comfortable spending time with yourself, you need to be comfortable making friends with complete strangers, be culturally aware and empathetic and much more.

I tell most people to do a stint of 1-3 months of travel before committing to a year long journey, or longer.

Q2. What is the difference in mindset between someone who is willing to take the leap to start their own business is vs someone who is stuck in their 9-5 job. What then is the first step towards the mindset change? 

A mindset that is no longer encapsulated in fear, that’s willing to take a risk and be ok without the outcome, and likely a mindset that can no longer take the status quo and is ready for a radical change.

When I quit my job with no safety net and no idea what I was going to do next, I simply knew I could not stay a day longer in my soul sucking job. That was enough for me. I appreciate that’s not normal or going to work for everyone.

The next step towards the mindset change is to look at where you want to be, whose life/ biz you’d like to emulate, and start reading up on what they did to get there.

Surround yourself with people who think differently from you, and have achieved what you want to achieve. Learn from them. Ask them a lot of great questions. And then act on what you learn when you’re ready.

Also you can check out my course Master Your Mindset  – How to get unstuck, crush your limiting beliefs and achieve rapid transformation, with Performance Coach Osmaan Shariff.

Q3. Would you say it’s crucial for someone who turns location-independent to have a home-base to return in case they ever change their mind or get tired (or their business goes belly up)? More specifically, do you think location-independent entrepreneurs should own property before they start their journey?

No it’s not crucial. I never had one. It does depend on how much you value security and having a base. But if you can keep a room rented out that you can return to, or have an option to store some stuff you can return to, it’s a good plan in case it all turns to custard.

That’s an interesting second question. I think it’s wise to own property at any point in your life. I’ve been able to buy three on my travels, all while living out of a suitcase still. They now provide a significant chunk of my residual income and are great assets.

Q4. Is saving up for retirement a viable option for Digital Nomads who no longer have residency in one place and may not be eligible for various government pension schemes? Is it even an issue within the DN community, or do people no bother with it at all? 

That’s a valuable question and one I hadn’t fully considered before.

In my opinion, it’s easier than ever to save money as a digital nomad, provided you live within your means, for the very reason that you don’t have to pay mortgages, and baseline infrastructure costs like wifi, cable, electricity that you would if you had a home base.

Also if you travel for long enough away from your home, depending on the country you’re from, you may find yourself in the enviable position of being a non-tax resident, in which case, so long as you stay nowhere for longer than 3 months, you won’t have to pay tax.

I’m not a legal or financial expert, but when I found myself in this position, I did hire a lawyer and immigration specialist to make sure I wasn’t doing anything unlawful – and I wasn’t. It was a great period to save money and buy property.

In terms of pension schemes, I guess I was not concerned about this, as the minute I quit my job I realized I would not be going back and so would be responsible for my own income and retirement savings.

I’d ask an expert on this. But I can pretty much guarantee you won’t be a digital nomad all your life, and when you’re residing in your country of choice again, after a period of time, you’ll become eligible for a pension.

Handy resource: Listen to my podcast [248] Navigating The Tax Laws For a Location Independent Business with David McKeegan 

Q5. Does it happen sometimes that you consider going back to a stable contract-based job, even if it meant to travel less and be less free in life?

Yes. Absolutely. Being an entrepreneur is one of the most demanding and rewarding roles I’ve ever had.

But sometimes I want to apply my skills and experience to other worthy organizations and social enterprises I know I could help, rather than to my own business.

I also think there’s a lot of freedom through discipline and structures, and that sometimes within limitations, you find a new form of freedom.

I’ve had too much freedom at many times in my life and for some, that can be debilitating – I kid you not. Too much choice can leave you paralysed.

Handy Resource: Read when Too Much Change is Dangerous.

Q6. What are your best financial tips for digital nomads?

Just being a digital nomad in my mind is a great financial move, especially if you live minimally while on the road, but enjoy your life.

Depending on where you travel (Asia, South America, parts of Europe), you can live like a king or queen for very little.

Other than that, become adept at Travel Hacking to use airpoints and rewards programmes to get cheap or free flights and accommodation.

Q7. What is the most mentally challenging part about being a digital nomad?

The constant decision making and not always knowing what’s next, as it’s not always within your control.

When I started out in 2009, there was no AirBnb, Uber or Remote Year. You had to make every decision for every area of your life, every day.

These days I think it’s downright easy to travel the world. There are built in communities to hang with, places like Roam that are coworking and coliving and learning rolled into one.

So many decisions and challenging factors have been removed- thankfully – to make your life as a digital nomad or location independent that much easier.

The other main thing that people do struggle with is a sense of not knowing. In many ways you’re a total free spirit as a digital nomad, and this can work in your favour but also against you if you value certainty as one of your 6 human needs.

Handy resources to help: Read Goodbye Loneliness – How to Meet New Friends as a Suitcase Entrepreneur.

Watch Is Co-Working The Cure For Entrepreneurial Loneliness?

Q8. I know you don’t have a crystal ball, but where do you see the digital nomad lifestyle in both 10 and 20 years? 

Oooh great question. And how do you know I don’t have a crystal ball? 😉 – I don’t. But it would be cool.

I think the future of work is a movement that will continue to mature. More and more people will become nomadic or remote workers, and digital nomads – or location independent and remote workers, will be more norm, not the exception.

In 10-20 years – it’s happening already, there will be more hubs of people around the world who travel to be with others they like, so there will be roaming communities of like-minded nomads.

That’s my gut feel from what I’ve seen and witnessed as a ‘pioneer’ in this space (media’s words not mine). I’m really curious to see how it plays out actually.

Q9. Can and how to make that initial major leap to the nomadic lifestyle from having a stable 9-5 job?

Yes you absolutely can. How?  In short quit your job and buy a one-way ticket to somewhere cool. Preferably have three months back up funds!

Q10. How do you ensure income stability as a digital nomad?

Design and build a business with multiple revenue streams, one of which is recurring like a subscription base or membership.

Handy resource: Watch my video on how to turn your content into multiple revenue streams.

Q11. Not many people like to talk about this, but sometimes your own location-independent business just doesn’t work out and you’re left with no clients and possibly no cashflow from your business. What would you recommend to someone whose venture is failing after they’ve already become location-independent? 

Look at what’s been working in the past and how you can get that back on track, then strip out all the other areas so you’re left with a singular focus to build on.  

Alternatively learn the lesson from what’s led you to this point of failure, and use it to start a new venture where your skills and experience can be reapplied in a better way.

Third alternative is get an interim job or contract while you build your next side hustle.

Q12. What helps you get back on track when you experience difficulties in earning money: any motivation tips, quotes by other people or rituals for those cases? 

Looking at my 1 Page ‘Miracle’ Biz Plan to see what my plan was for making money – and to see if I am in fact sticking to the plan or haven’t followed through on my priorities!

Here’s the free template  (it’s in my book and on my book website too).

If you don’t have a financial/ profit plan then that’s probably a big part of the problem!

You need to get really clear on the products and services you offer, what they’re worth and how many clients you need to be sustainable to cover your monthly expenses.

What helps me get back on track is coming back to a plan of attack and then taking baby steps to make it work.

That and listening to pump up music and doing the hard work – like reaching out to previous clients, getting in front of new one, doing whatever it takes to bring in revenue (so long as it’s in alignment with my values and business needs).

Q13. Would you advise aspiring digital nomads to start with freelancing, passive business or startups?

Freelancing is a great way to be able to travel and take on projects adhoc to suit your lifestyle and give you more flexibility.

It can also lead into being a business. Passive revenue takes much longer to build. You need to plan for that so you aren’t left short of cashflow.

Q14. What kinds of digital nomad communities would you recommend a nomad to join?

Online or offline? You’re already in a great one by the looks of it 🙂

DNX (Digital Nomad Festival and Community) is another great one, Dynamite Circle, Digital Nomad Girls, Remote Year, Hacker Paradise  – there are so many these days it’s hard to keep track!

Choose one that makes you feel welcome and fits with where you’re at.

Q15. What are some of the most curious things you’ve seen as you travel?

One of my favourite was in Cambodia – it’s seen on postcards a lot now, but to me, the first time I saw a family of 5 on a scooter with a massive bunch of bananas too was pretty special.

I think this deserves a blog post – that’s curated by everyone in this community! That would be fascinating.

Q16. What’s your favourite off the radar nomad location that will likely be a hotspot in a few years?

It used to be Portugal, and Lisbon. But now that’s a massive hub. Same with Bali. Then it became Colombia (Medellin).

I’d like to see some South American countries in the mix and hope that Brazil will be. Plus. I’m bias, but New Zealand.

Looking to Peniche town in Portugal

Q17. In what ways do you think travel has changed you as a person?

In every way. It’s a wonderful education, it’s humbled me, challenged me and made me way more open-minded and respectful of cultures and people from such diverse backgrounds, to name but a few ways.

I notice it most when I meet people who’ve never travelled outside their own town or city and whose minds are yet to be opened to all the big wide world has to show and teach them.

Travel – if you let it, gives you depth, meaning, challenge, wonder and new insights into your own world view. It’s like applying a different lens to your existing world and forever changing the way you see through it.

Q18. Any travel hacks you can offer?

Yes! Get a credit card that has a great rewards programme and then put every travel and business expense on there, even your contractors, rack up the points and transfer them to an airline program you use most often.

There a number of credit cards that offer tens of thousands of points as a signup bonus which can eventually be redeemed for flying miles. You can find a full list of the best ones here.

The basic premise is use your credit card for EVERY single purchase, pay it off each month in full and rack up miles for every dollar spent, then you can redeem them on major airlines for free flights or hotel stays, or flight or hotel upgrades.

Another way to gain flight miles is to keep up to date with the bonuses that airlines and hotel accommodations are offering. Sometimes just by filling out a survey, they’ll give you 500 frequent flyer miles.

There a number of deals, and it can be tough to keep up with them all, which is why Chris created the Travel Hacking Cartel, which can teach you the nuts and bolts of travel hacking while also sending you notifications of the deals, making it dead easy to travel hack.

Q19. Do you plan on traveling to every country in the world?

Once I thought I did, but then my friend Chris Guillebeau did and it looked exhausting. 70 is enough for now.

I’d like to probably get to 100, but it’s more about quality time in the country than racking up numbers, and going to each country to truly experience it.

Q20. How do you deal with jetlag especially when traveling quickly?

1Above – anti jetlag pill you put in water – works great. Also great for post a heavy sports game or workout.

Otherwise lots of water, eating on the plane at the same timezone you’re going to so you get in sync before you land.

Q21. How long do you usually stay in one place?

I think when I travelled I was nuts. I basically never stayed longer than a few days or weeks for like 5 years of consistent travel.

However I did originally spend 5 months in Buenos Aires when I started out, then 2 months in Amsterdam and Berlin. Then bounced!

I’d do slow travel if I were to do it all again, 2-4 months in one place to truly get to know it.

Q22. What’s your favourite country to live in so far?

Aside from New Zealand, Portugal. I feel like it’s the European New Zealand.

Friendly people, proud but not arrogant. Great coastline for surfing, swimming, sailing and more.

Wonderful food and wine, and wineries. Smaller population, easy to get around, lots of untouched and less populated parts. Easy going and lots of festivals, art and culture.

Q23. How big is your suitcase and how are you able to stay in countries with extremely different weather, like deep winter and intense summer?

I still have my original Rimowa Salsa Air suitcase they sponsored me in 2010! It’s amazing. Check out this YouTube video from 7 years ago of me unpacking it – it’s a crack up.

It’s a medium size and I love it. It’s supremely light. I layer clothes, I don’t take many shoes and buy and then donate what I need to friends or strangers when I leave a season or country.

Q24. What are your must-haves in every country that you live in?

I talk all about this in my Suitcase Entrepreneur book. Multi adaptor plug, ear plugs, jandals/ flip flops, running shoes, sunscreen, sunglasses, light wrinkle free outfits. 2 weeks worth of clean underwear!

Q25. What’s the biggest culture shock you’ve experienced in your years working overseas?

First visit to Laos I think when they had no running water, toilets you poured water into, candles once the generators were turned off at 5pm.

Pets, families and wildlife all living harmoniously in basic thatched houses by the river. Loved it though!

Q26. Do you have a daily routine that you stick to especially when you move around a lot?

Yes, I did a vlog on YouTube on it and turned it into a free eBook. I love this routine and it’s doable while traveling or at home.

Q27. How did you go about lessening your workload? Was it through automation or hiring workers?

Both actually. My new book The Freedom Plan pretty much was written to show people who to do this for yourself.

Also in my free video series that brings the book to life, I take you through the Four Lists to Freedom Exercise, so you can see exactly what you need to delegate, what you shouldn’t be doing, and what you can start outsourcing!


I hope you enjoyed this Q&A post and if you have any other questions, leave them below and I’ll answer them in the comments. Plus share your own experiences!